A self-described lover of the state constitution, Huber says he has a soft spot for the state motto, “Forward.”

His father, Roy Huber, was a technician for American Motors and Chrysler for 25 years. He is also the namesake of the Roy boot, but more on that later. His mother, Joan, has been a secretary in the Kenosha Unified School District for the past 20 years. Like Huber, they too are Wisconsin-made people.

So, how does the son of Wisconsin-to-the-core parents open up one of the best men’s clothing stores in the country, if you believe the hype? Simple. Huber loves jeans. He loves hard work. He knows what he wants, and how to get it. And? He’s got that Midwestern charm.

“People from the coasts come to Wisconsin and say, ‘Everyone is so friendly.’ No one’s waving to you and saying ‘hi’ to you in New York walking down Broadway … in Wisconsin if you’re [on a motorcycle] (which he often is) on a country road, every guy will wave to each other,” Huber says.

Huber is the proud owner of a 1982 Honda CB-750 f. It may not be a Harley, but that is a man’s bike. Last summer, while riding his Honda the engine blew up. He was wearing a white t-shirt, a helmet and denim. Just denim? Unperturbed, he replied, “Really solid, 14oz Japanese denim.” No leather. (Men, take note.)

“Very James Dean,” I comment in response to the white ‘T’ and jeans.

“I wear a lot of white t-shirts and jeans on a motorcycle,” he responds. “I’d say more Steve McQueen than James Dean. James Dean always drove Porsches, he drove motorcycles too, but Steve McQueen — he’s the man!”

Huber has built his business on good old-fashioned Wisconsin friendliness, and a heaping spoonful of cool, a la Steve McQueen.

Context’s small, devoted staff, self-described fantastic eye for spotting good brands and excellent customer service are some of the characteristics he says sets them apart from other men’s clothing stores in the country.

“We are tiny. It’s basically a three-man operation. So when you answer an e-mail at four in the morning, its like holy shit. Do you guys sleep?” Huber says.

Huber and I are sitting in Madison’s, a bar down the block from Context and named after the city he’s built his store around. He’s drinking a local microbrew (go figure) and telling me about a conversation he had with his father about ‘The Roy’-a boot named after his father.

“Hey. I named a boot after you,” Huber says to his Dad, “and it’s a fucking awesome boot.”

The Roy is a joint venture between Context and Alden, an American shoe company that manufactures 100 percent of their goods by hand in the USA. They approached Context to make the ultimate denim boot. Enter the Roy.

Huber’s father has had an important influence on why and how he understands Wisconsin men.

“My father [has] always worked with his hands. He could fix the car, fix the motorcycle. He’s very much instilled in me the value in quality craftsmanship and of American craftsmanship. He’s a very Midwestern dude,” Huber says. It was with this in mind that he created the Roy.

Huber loves America. His commitment to sourcing American-made garments and footwear borders on fanatical. Blame it on his father, he says, but transparency of production is important to him. So when Alden came knocking, it was like he’d just won the showcase on the Price is Right.

“Sam and I were amazed, like floored. Because [Alden is] one of the best companies, it’s like one of the best companies period,” Huber says.

Please take note. The Roy, Context’s best selling product, is $445, and it is currently backordered until March. According to Huber, this boot can take a beating, which is why it’s so popular here in Wisconsin.

“Midwesterners wear their clothing differently,” Huber says. “They buy less clothing and expect that clothing to last. They’re more likely to say why is this $200? I’m not fucking buying this. It’s $200?! In LA they’re gonna be, ‘What’s the hottest shit? I want it!’”

James Bickers, a longtime close friend of Huber’s and a frequent patron of Context, knows Huber and his father well, and recognizes Huber’s father’s influence on the way he runs the store.

“His dad has worked his whole life and is still dynamic,” Bickers says. “What [Huber and his father] each did to make a living couldn’t be more different, but the style with which they pursue it is so similar. He just learned a work ethic, you commit to something and you see it through.”